In the blink of a glitter-coated eye, Miley Cyrus went from the unknown spawn of a nineties crooner famous for wearing overalls and a mullet to the face of the billion-dollar Hannah Montana franchise. But nothing lasts forever: Hannah allegedly has just one more guaranteed season, and Miley wants to transition into “serious acting,” reportedly via a custom-written Nicholas Sparks schmaltzfest in the vein of The Notebook. In other words, 16-year-old Miley officially has entered that awkward phase between coasting on her tween-idol charms and slowly disassociating herself from Disney tripe in order to be taken seriously. What better way to start redefining oneself than with wardrobe? This past month, as she globe-hopped to six premieres for Hannah Montana: The Movie, we tried to gauge how — or if — her clothes peddled a more mature Miley to the world. The results were, much like Hannah’s ratty blonde wig, totally all over the place.

Photo: Getty Images

There’s a saying that you ought to dress for the job you want, not the job you have; judging from these two looks, Miley is gunning for a gig on a generic CW teen drama. She’s leggy and adorable in a teal fringed dress and leather jacket at the Hannah Montana Los Angeles premiere, but if you squint your eyes, you could easily imagine that outfit on the likes of Sophia Bush or one of the girls from 90210. The ruffled pink skirt Miley paired with a boob-tastic white tank at the Rome premiere is much worse, recalling Ashley Tisdale on a bad day in the middle of the High School Musical juggernaut. Surely the last thing Miley needs is to remind us of her Disney roots.

Photo: Getty Images

These two youthfully relaxed outfits do a better job of bridging the gap between being Disney-fied and dignified, but mimicking the polished flower-child aesthetic of a Nicole Richie should not be done without adult supervision. For starters, the kid desperately needs a hair wrangler. Her tresses are needlessly molesting the silver frock Miley brought out in Munich, to the point where it almost gets lost behind scraggly strands, and the purple could’ve been so much more adult and regal with about three fewer bracelets and a loose updo. And a lesson on posture. Still, on the whole, both are a refreshing step away from the Miley of yore, who never met a sequined tank minidress she didn’t try to wear.

Photo: Getty Images

We applaud Miley for taking a few risks on her world tour, as if she decided to take at least temporary inspiration from successful actresses and fashion darlings Kate Bosworth and Diane Kruger. It paid off with the edgy silver Hervé Léger minidress she wore in London, possibly the best look Miley’s ever trotted out in public: fresh, current, and sophisticated, while seeming effortlessly so. We know; we’re stunned, too. But just as big risks often reap big rewards, they can also turn you into Stumpy McNoNeck, which is less likely to get you a meaty acting role than it is a reputation for playing dress up in your mother’s closet. And so it was in Paris, where poor Miley fell flat in a ruffled Dolce & Gabbana printed number whose proportions ate her alive. It’s possible that dress would look good on someone, but Miley is not that person.

Overall, Team Cyrus gets an A for effort — a girl can’t look like she just fell out of Hot Topic forever, and four of the six outfits are at least flattering and polished. And while the haphazard execution at first struck us as directionless, in the end it might be exactly what Miley needs: After all, the last time someone shoved a teenage girl into a direction she didn’t choose for herself, we got Britney beating the paparazzi with an umbrella and shaving her head. Compared with that, we’ll take a slow evolution any day.

Related: The Very Scary Clothes at the Hannah Montana Premiere

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